US4724264A - Fluoroalkoxy cyclic phosphonitrile esters - Google Patents

Fluoroalkoxy cyclic phosphonitrile esters Download PDF

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US4724264A
US4724264A US06/856,360 US85636086A US4724264A US 4724264 A US4724264 A US 4724264A US 85636086 A US85636086 A US 85636086A US 4724264 A US4724264 A US 4724264A
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oil
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Yoshifumi Nakacho
Yuji Tada
Tetsuya Yagi
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OTSUKA KAGAKU A CORP OF JAPAN KK
Otsuka Chemical Co Ltd
Matsumura Oil Research Corp
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Otsuka Chemical Co Ltd
Matsumura Oil Research Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/049—Phosphite
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/32—Wires, ropes or cables lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • the present invention relates to novel fluoroalkoxy cyclic phosphonitrile esters.
  • Petroleum lubricant heretofore widely used as rotary pump oil is prepared from a petroleum lubricant fraction having a kinematic viscosity of 30 to 150 centistokes at 40° C., by refining the fraction by fractionation such as molecular distillation.
  • the lubricant is very low in vapor pressure, has high heat resistance and meets various requirements.
  • the rotary pump oil for the dry etching apparatus for producing semiconductors is exposed to an active gas such as a gas mixture of tetrafluoromethane (Flon-14) and oxygen, so that the conventional petroleum rotary pump oil, if used, is prone to a rise of viscosity or deposition of sludge within a short period of time, therefore needs frequent replacement and requires much time and labor for the maintenance of the rotary pump.
  • an active gas such as a gas mixture of tetrafluoromethane (Flon-14) and oxygen
  • the apparatus which are presently used and in which an active gas is used or needs to be discharged include dry etching apparatus, semiconductor manufacturing apparatus which are typicallly ion implantation apparatus and plasma chemical vapor deposition (CVD) apparatus, CVD apparatus for producing cutting tools of cemented carbides, apparatus for producing halogen lamps, degassing apparatus for preparing iron and steel, and apparatus for producing electrically superconductive materials.
  • dry etching apparatus semiconductor manufacturing apparatus which are typicallly ion implantation apparatus and plasma chemical vapor deposition (CVD) apparatus
  • CVD apparatus for producing cutting tools of cemented carbides
  • apparatus for producing halogen lamps apparatus for producing halogen lamps
  • degassing apparatus for preparing iron and steel
  • electrically superconductive materials for producing electrically superconductive materials.
  • active gases examples include phosphine, arsine, diborane, hydrogen selenide, arsenic trichloride, silane, silicon tetrachloride, hydrogen chloride, dichlorosilane, Flon-14, ammonia, phosphorus pentafluoride, silicon tetrafluoride, carbon tetrachloride and oxygen. These gases are used singly, or at least two of them are used in combination.
  • the oil must have a very low viscosity, a low vapor pressure, the satisfactory low-temperature characteristic of being minus tens of degrees in solidifying point, and heat resistance to withstand the heat developed from the operation of the pump, and all of these requirements need to be fulfilled by a single chemical structure.
  • these are characteristics which conflict with one another and nevertheless need to be realized at the same time.
  • a reduced molecular weight provides a lower viscosity but results in a higher vapor pressure.
  • Attempts to obtain low-temperature characteristics tend to lower the upper limit of temperatures where satisfactory oil properties are available.
  • difficulties are encountered in molecular design.
  • the chemical substance obtained with these characteristics must further have exceedingly high stability against chemical substances such as acids and alkalis, especially active gases. Extreme difficulties are therefore encountered in preparing a novel chemical substance having all of these required characteristics in good balance.
  • An object of the invention is to provide a compound which is excellent in heat resistance, viscosity, compatibility with resins and low-temperature characteristics, as well as in lubricant performance and resistance to active gases.
  • the present invention provides a fluoroalkoxy cyclic phosphonitrile ester represented by the formula (1)
  • (CF 2 CF 2 )m is a single segment of the unit (CF 2 CF 2 ) multiplied by an integer or indicates conjoint presence of segments having different chain lengths and each comprising the unit (CF 2 CF 2 ) multiplied by an integer
  • m is 2 in the case of the single segment or, in the case of the presence of segments of different chain lengths, represents the average of the chain lengths, means the average number of repeating units (CF 2 CF 2 ) and is in the range of 1.3 ⁇ m ⁇ 2.8
  • l is in the range of 2n-1 ⁇ l ⁇ 1
  • n is the number of repeating PN units of the phosphonitrile cyclic skeleton, or represents the average number of repeating PN units and is a real number in the range of 3 ⁇ n ⁇ 4.3 when rings of different numbers of repeating units are conjointly present.
  • the fluoroalkoxy cyclic phosphonitrile ester of the formula (1) is a novel compound not disclosed in literature and is prepared from an oligomer of phosphonitrile halide and a fluoroalcohol as described in the example given later.
  • the cyclic phosphonitrile ester of the formula (1) is prepared by reacting an oligomer of phosphonitrile halide of the formula ##STR1## wherein X is halogen atom, n represents the average number of repeating PN units and is a real number in the range of 3 ⁇ n ⁇ 4.3 when rings of different numbers of repeating units are conjointly present, a fluoroalcohol of the formula
  • m means the average number of repeating units (CF 2 CF 2 ) and is in the range of 1.3 ⁇ m ⁇ 2.8.
  • Examples of useful oligomers of phosphonitrile halides are phosphonitrile chloride trimer, phosphonitrile chloride tetramer and a mixture of such oligomers.
  • Examples of useful fluoroalcohols are 1,1,3-trihydroperfluoropropanol, 1,1,5-trihydroperfluoropentanol and like 1,1, ⁇ -trihydroperfluoroalcohols, mixtures of such an alcohol and 2,2,3,3,3-pentafluoropropanol.
  • the fluoroalkoxy cyclic phosphonitrile ester of the formula (1) is prepared by reacting sodium or like alkali metal with a mixture of at least one 1,1, ⁇ -trihydroperfluoroalcohols and 2,2,3,3,3-pentafluoropropanol to obtain an alcoholate and subsequently reacting the alcoholate with an oligomer of phosphonitrile halide.
  • the latter is usually used in an amount of about 2.02 to 2.25 moles per one unit mole of the former as calculated in terms of PNX 2 .
  • the fluoroalcohol is preferably converted into an alcoholate beforehand by the reaction thereof with sodium or like alkali metal.
  • the reaction is conducted preferably in an organic solvent such as benzene, toluene, xylene and like hydrocabons, ethyl ether, isopropyl ether, tetrahydrofuran, dioxane and like ethers, etc.
  • the reaction temperature is preferably from about 10° C. to reflux temperature, and particularly from room temperature to 100° C.
  • the reaction time is not particularly determined but is preferably about 2 to 10 hours.
  • the present desired compound can be isolated and purified by a known method and for example is washed with water, dried, concentrated and then purified by a precision fractionator, etc.
  • fluoroalkoxy cyclic phosphonitrile esters represented by the formula (1) preferable are, for example, mixed fluoroalkoxytetraphosphonitrilates of the formula (1) wherein n is 4, m is 2 and l is in the range of 1 ⁇ l ⁇ 7.
  • the compounds of the present invention are useful as nonflammable lubricants, hydraulic oils, etc., especially as rotary pump oils.
  • the ester When l is 0, the ester has a high viscosity at room temperature and requires an excessively great torque for starting pumps, possibly causing damage to the electric motor. If l is 8, the ester is solid at room temperature and is unusable as a fluid. Accordingly, such esters are not suited to use.
  • FIG. 1 is a diagram showing the proton NMR spectrum of one of the compounds obtained in Example 1;
  • FIG. 2 is a diagram showing the IR absorption spectrum of one of the compounds obtained in Example 1;
  • FIG. 3 is a diagram showing the vapor pressure charts of some of the compounds obtained in Example 1;
  • FIG. 4, FIG. 5 and FIG. 6 are diagrams showing proton NMR spectra of some compounds obtained in Example 2;
  • FIG. 7 is a diagram showing the IR absorption spectrum of one of the compounds obtained in Example 2.
  • FIG. 8 is a diagram showing the proton NMR spectrum of the compound obtained in Example 3.
  • FIG. 9 is a diagram showing the IR absorption spectrum of the compound obtained in Example 3.
  • Boiling point 209° ⁇ 211° C./0.3 mmHg
  • Boiling point 201° ⁇ 203° C./0.3 mmHg
  • Boiling point 168° ⁇ 170° C./0.3 mmHg
  • Refractive index (n, 20° C.): 1.3460
  • Boiling point 157° ⁇ 159° C./0.3 mmHg
  • FIG. 1 shows the proton NMR spectrum of pentakis(2,2,3,3,3-pentafluoropropoxy)tris(1,1,5-trihydroperfluoropentyloxy)cyclotetraphosphonitrile among other compounds obtained as above.
  • the spectrum shows absorption characteristic of the 5-position hydrogen coupled with fluorine at 5.75, 6.40 and 7.05 ppm, with the sole difference in the integral strength ratio of absorption by the 1-position hydrogen at 4.5 ppm, compared with NMR spectra of other six compounds.
  • FIG. 2 shows the IR absorption spectrum of tetrakis(2,2,3,3,3-pentafluoropropxy)tetrakis(1,1,5-trihydroperfluoropentyloxy)cyclotetraphosphonitrile obtained as above.
  • the spectrum reveals absorption by the skeleton of cyclophosphonitrile tetramer at 1350 cm -1 .
  • FIG. 3 is a diagram showing the vapor pressure charts of tris(2,2,3,3,3-pentafluoropropoxy)pentakis(1,1,5-trihydroperfluoropentyloxy)cyclotetraphosphonitrile, tetrakis(2,2,3,3,3-pentafluoropropoxy)tetrakis(1,1,5-trihydroperfluoropentyloxy)cyclotetraphosphonitrile and pentakis(2,2,3,3,3-pentafluoropropoxy)tris(1,1,5-trihydroperfluoropentyloxy)cyclotetraphosphonitrile.
  • a 605 g quantity of an oily crude product was obtained by preparing an alcoholate in the same manner as in Example 1, adding dropwise a solution of 178 g of phosphonitrile chloride trimer in toluene to the alcoholate, and reacting and after-treating the mixture in the same manner as in Example 1.
  • the product was distilled at 130° to 195° C./0.75 to 0.03 mmHg and thereafter fractionated by the precision fractionator HP-9000B. The fractions were checked to identify the following compounds produced.
  • Boiling point 167° ⁇ 169° C./0.3 mmHg
  • Boiling point 142° ⁇ 144° C./0.3 mmHg
  • Boiling point 130° ⁇ 132° C./0.3 mmHg
  • FIGS. 4, 5 and 6 show the NMR spectra of bis(2,2,3,3,3-pentafluoropropoxy)tetrakis(1,1,5-trihydroperfluoropentyloxy)cyclotriphosphonitrile, tris(2,2,3,3,3-pentafluoropropoxy)tris(1,1,5-trihydroperfluoropentyloxy)cyclotriphosphonitrile and tetrakis(2,2,3,3,3-pentafluoropropoxy)bis(1,1,5-trihydroperfluoropentyloxy)cyclotriphosphonitrile, respectively, among other compounds obtained as above.
  • FIG. 7 shows the IR absorption spectrum of tetrakis(2,2,3,3,3-pentafluoropropoxy)bis(1,1,5-trihydroperfluoropentyloxy)cyclotriphosphonitrile.
  • Example 2 Into the same reactor as used in Example 1 were placed 178 g (0.384 mole) of phosphonitrile chloride tetramer and 1000 ml of toluene, and the tetramer was completely dissolved. To the solution was added dropwise an alcoholate prepared from 480 g (2.06 moles) of 1,1,5-trihydroperfluoropentanol and 45.5 g (1.98 moles) of sodium in 1000 ml of toluene. The mixture was reacted at 50° C. for 4 hours.
  • the compound obtained was identified as bis(2,2,3,3,3-pentafluoropropoxy)bis(1,1,3trihydroperfluoropropoxy)tetrakis(1,1,5-trihydroperfluoropentyloxy)cyclotetraphosphonitrile by gas chromatography, mass analysis and proton NMR spectrum.
  • the compound had a refractive index of 1.3567 at 20° C.
  • FIG. 8 shows the proton NMR spectrum of the product, and FIG. 9 the IR absorption spectrum thereof.
  • An alcoholate was prepared in the same manner as in Example 1 from a mixture of 63 g of 2,2,3,3,3-pentafluoropropanol, 56 g of 1,1,3-trihydrotetrafluoropropanol and 98 g of 1,1,5-trihydrooctafluoropentanol and then reacted with phosphonitrile chloride tetramer.
  • the reaction mixture was treated in the same manner as in Example 1 to collect 235 g of a fraction at 160° to 185° C./0.03 mmHg.
  • compound B a colorless transparent oily substance which was 1.73 in specific gravity (20° C.), 285 cps in viscosity (40° C.) and -35° C. in pour point.
  • the product (hereinafter referred to as "compound C”) was 1.74 in specific gravity (20° C.), 340 cps in viscosity (40° C.) and -35° C. in pour point.
  • Compound A was poured into a mechanical vacuum pump completely cleaned with a solvent.
  • the oil temperature, degree of vacuum and power consumption were measured on start-up and during one-week continuous operation.
  • Table 1 shows the results, which reveal that the compound is usable as a vacuum pump oil without any problem.
  • Compound B was poured into a mechanical vacuum pump completely cleaned with a solvent, and the pump was used for operating an experimental plasma generator wherein a mixture of Flon-14 and hydrogen was used. No abnormalities were found in the motor current value during operation for 30 days.
  • the oil was drawn off and checked, a small amount of reddish brown liquid was found on the oil.
  • the oil had a viscosity of 280 cps at 40° C., while the oil before use had a viscosity of 285 cps at the same temperature, hence almost no change in viscosity.
  • IR, NMR and MS (mass spectrum) analyses revealed no difference between the used oil and the fresh oil.
  • the reddish brown liquid which appeared attributable to the plasma or the etched work, caused no trouble to the operation of the rotary pump.
  • a mechanical vacuum pump (exhaust rate 960 liters/min, amount of oil 2.2 liters) was operated with compound A placed therein for a dry etching apparatus for etching silicon substrates with use of a mixture of Flon-14 and oxygen in a semiconductor manufacturing process.
  • Fluorine rubber which is frequently used for applciations where resistance to chemicals is required was tested for resistance to the present compound.
  • a Viton O-Ring V#4640, 4DG-30, product of Asahi Chemicals Co., Ltd., was immersed in compound A at 80° C. for 15 days and thereafter checked for the resulting change in volume. The volume increase ratio was 2.2%.
  • the above procedure was repeated using in place of compound A hexakis(1,1,5-trihydrooctafluoropentyl)triphosphonitrilate ("active gas resistant rotary pump oil A" disclosed in Japanese Unexamined Patent Publication No. 1983-164698).
  • the volume increase ratio was 9.55%.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Health & Medical Sciences (AREA)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5015405A (en) * 1989-10-05 1991-05-14 The Dow Chemical Company (Fluorinated phenoxy)(3-perfluoroalkylphenoxy)-cyclic phosphazenes
US5073284A (en) * 1989-12-07 1991-12-17 Ethyl Corporation Phosphonitrilic mixed esters
US5099055A (en) * 1989-10-05 1992-03-24 The Dow Chemical Company (Fluorinated phenoxy)(3-perfluoro-alkylphenoxy)-cyclic phosphazenes
US5230964A (en) * 1989-10-05 1993-07-27 The Dow Chemical Company Magnetic recording media a comprising magnetic particles binder and (fluorinated phenoxy)(3-perfluoroalkylphenoxy)-cyclic phosphazene lubricant
US20050142296A1 (en) * 2003-12-30 2005-06-30 3M Innovative Properties Company Substrates and compounds bonded thereto
US20070065490A1 (en) * 2003-12-30 2007-03-22 Schaberg Mark S Substrates and compounds bonded thereto

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1256304B (it) * 1992-11-10 1995-11-30 Ausimont Spa Derivati fosfazenici e loro impiego come stabilizzanti per oli e grassi a base di perfluoropolieteri
JP5034027B2 (ja) * 2005-10-03 2012-09-26 株式会社Ｍｏｒｅｓｃｏ パーフルオロポリエーテル化合物、およびこれを用いた潤滑剤ならびに磁気ディスク

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3888800A (en) * 1971-10-13 1975-06-10 Firestone Tire & Rubber Co Preparation of phosphazene polymers
US4601843A (en) * 1985-04-02 1986-07-22 Borg-Warner Chemicals, Inc. Phosphazene based functional fluid compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2876247A (en) * 1957-07-03 1959-03-03 Olin Mathieson Chemcial Corp Polymeric polyfluoroalkyl phosphonitrilates
JPS6046154B2 (ja) * 1982-03-24 1985-10-14 株式会社松村石油研究所 耐活性ガス性ロ−タリポンプ油

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3888800A (en) * 1971-10-13 1975-06-10 Firestone Tire & Rubber Co Preparation of phosphazene polymers
US4601843A (en) * 1985-04-02 1986-07-22 Borg-Warner Chemicals, Inc. Phosphazene based functional fluid compositions

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Austin et al, "Macromolecules", (1983), 16, 719-722.
Austin et al, Macromolecules , (1983), 16, 719 722. *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5015405A (en) * 1989-10-05 1991-05-14 The Dow Chemical Company (Fluorinated phenoxy)(3-perfluoroalkylphenoxy)-cyclic phosphazenes
US5099055A (en) * 1989-10-05 1992-03-24 The Dow Chemical Company (Fluorinated phenoxy)(3-perfluoro-alkylphenoxy)-cyclic phosphazenes
US5230964A (en) * 1989-10-05 1993-07-27 The Dow Chemical Company Magnetic recording media a comprising magnetic particles binder and (fluorinated phenoxy)(3-perfluoroalkylphenoxy)-cyclic phosphazene lubricant
US5073284A (en) * 1989-12-07 1991-12-17 Ethyl Corporation Phosphonitrilic mixed esters
US20050142296A1 (en) * 2003-12-30 2005-06-30 3M Innovative Properties Company Substrates and compounds bonded thereto
US20070065490A1 (en) * 2003-12-30 2007-03-22 Schaberg Mark S Substrates and compounds bonded thereto
US7658994B2 (en) 2003-12-30 2010-02-09 3M Innovative Properties Company Substrates and compounds bonded thereto

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Publication number Publication date
JPH0572916B2 (cs) 1993-10-13
EP0204144A3 (en) 1987-01-28
DE3662399D1 (en) 1989-04-20
EP0204144A2 (en) 1986-12-10
EP0204144B1 (en) 1989-03-15
JPS6253996A (ja) 1987-03-09

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